1. Field of the Invention
This invention relates to generally polymerizable monomeric compounds containing a terminal ureido group. More particularly, the invention is concerned with novel compounds having at one end thereof a cyclic or acyclic ureido group and at the other end a vinyl group, the terminal groups being connected through a selected linking structure as hereinafter described. The novel compounds of the invention can be designated by the general structural formula: ##STR3## wherein R is H or CH.sub.3, U designates a cyclic or acyclic ureido or thioureido group and L designates the linking structure, as hereinafter described.
2. Prior Art
There are disclosed in the prior art various monomeric compounds containing a ureido group at one end and an unsaturated ethylenic group at or near the opposite end, which unsaturated group may be the residue of an unsaturated mono- or di-carboxylic acid. Thus, the U.S. Pat. Nos. 2,881,155 and 2,881,171, there are described monomeric polymerizable compounds containing at one end a cyclic ureido group, and at the other end an acrylic or methacrylic acid radical linked through an alkyl amido group. These compounds correspond to the general structural formula ##STR4## wherein R is H or CH.sub.3 and A is an alkylene group having 2 or 3 carbon atoms.
Compounds of this type are prepared, for example, by condensing N-.beta.- aminoethyl-N-N'-ethyleneurea with an ester of an alpha haloacetic acid and then reacting the obtained intermediate with a salt of acrylic or methacrylic acid. The obtained compounds are capable of undergoing addition polymerization and condensation reactions.
Another type of compound containing a cyclic ureido structure at one end and at the other end the residue of an unsaturated dicarboxylic acid is described in U.S. Pat. No. 2,980,652; such compounds correspond generally to the formula: ##STR5##
Compounds of this type are also stated to be susceptible to both addition polymerization, by virtue of their unsaturation, and to condensation reactions by virtue of the heterocyclic nitrogenous rings.
Instead of condensing the N-aminoalkyl urea with an unsaturated dicarboxylic acid, a monocarboxylic acid, such as crotonic acid, is employed in U.S. Pat. No. 3,369,008 forming compounds of the general formula ##STR6##
By reacting the anhydride of a dicarboxylic acid with the N-hydroxyalkyl derivative of a cyclic urea, ester compounds are formed according to U.S. Pat. No. 3,194,792. These compounds correspond generally to the formula ##STR7## (m=zero to 9) Z=C.sub.2 to C.sub.8 alkylene group
R.sup.o =C.sub.2 to C.sub.3 alkylene group
The foregoing types of compounds are stated to be useful for one or more of the following purposes: as plasticizers for vinyl and acrylic resins and as anti-static agents; they may be reacted to form copolymers and interpolymers with monoethylenically unsaturated compounds, useful as warp sizes and for improving wet strength of paper; such copolymers also provide valuable coating compositions and bases for water-base paints, as well as binders for non-woven fabrics among other noted uses. Other suggested uses for certain of these compounds include the formation with various resin components of polymeric compositions having improved adhesion properties when employed in paints and coating compositions, particularly as applied to metals, glass and plastics.
A wide variety of monomers containing a ureido group of straight chain or cyclic type are disclosed in U.S. Pat. No. 3,300,429, including certain of those hereintofore described. According to that patent, improved coating and impregnating compositions are formed by admixing certain water insoluble addition polymers (1), such as vinyl ester or acrylic polymers, with a low molecular weight soluble ammonium salt of certain copolymers of ethylenically unsaturated carboxylic acids (2), and with a specified surfactant; when at least one of the components (1) or (2) comprises polymerized monomer units containing a ureido group. These coating compositions in the form of aqueous polymer dispersions and water base paints are stated to possess improved adhesion and penetration properties such as in their application to porous substrates including wool, textiles and non-woven fabrics as well as in their application to powdery or chalky surfaces.
In our copending patent application Ser. No. 709,677 filed July 29, 1976, there are described novel cyclic ureido monomers terminating at the opposite end in the residue of an allyl or methallyl ester as in ##STR8##
The compounds of said copending application, in contrast to the known cyclic ureido derivatives of the prior art, are characterized in that the carbonyl group in the chain linking the amino nitrogen of the N-aminoalkyl urea to the terminal ethylene group, is not directly attached to an ethylenic carbon atom.
In copending U.S. patent application Ser. No. 709,916 filed July 29, 1976, the synthesis of novel allyl succinamic ureido compounds is described. These compounds as well as those described in the companion copending application Ser. No. 709,677, are shown to be particularly useful as functional comonomers for imparting improved wet adhesion properties to emulsion systems containing vinyl ester polymers employed in paints and coating compositions. Other suggested uses for the described monomers of the aforesaid copending patent applications include: their use as such or as intermediates in resin modifiers, and as plasticizers, textile sizes, textile softeners, antistatic agents and wet strength paper resins.